


Oh, Pretty Little Thing

by miimsey



Series: Undertale Stories and Drabbles [1]
Category: Undertale (Video Game)
Genre: Alternate Universe - Mobtale (Undertale), Angst, Badass Reader, Blood and Violence, Ecto-Genitalia (Undertale), Ecto-Tongue (Undertale), Eventual Smut, F/F, F/M, Fluff, Hurt/Comfort, Implied/Referenced Alcohol Abuse/Alcoholism, Implied/Referenced Character Death, Implied/Referenced Child Abuse, Implied/Referenced Drug Use, Implied/Referenced Torture, M/M, Multi, Reader is a mage, it starts out all fine and dandy but it wont stay that way long, reader is a singer, you are warned
Language: English
Status: In-Progress
Published: 2019-01-20
Updated: 2019-03-11
Packaged: 2019-10-13 04:57:42
Rating: Not Rated
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 7,841
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17481614
Author URL: https://archiveofourown.org/users/miimsey/pseuds/miimsey
Summary: Life was never easy.Everything was up for the highest bidder, those who could pay their way to the top. Those who were unable to do the same were simply stuck at the bottom, scrambling to get out of the way of those who tried to squash them down. You were a street rat, a ruffian, a dirty child who had the whole world against her. Then, you got mixed up with the wrong people.Now you have the life of luxury, of comforts you can't afford, but it all comes with a price. Your walls are stained red, and the guilt you once felt was stamped out.After all, its a dog eat dog kind of world....right?





	1. just another night...or is it?

The muffled sounds of music and chatter was blocked through a thick glass separating the interior from the balcony.  
Sitting on the half-wall made of solid red stone, You look out at the faint twinkling lights of the stars that you could see through the thick smoke and smog that the city gave out. Your breath puffed warm in front of you, making soft clouds of breath show in front of you. Your hair and makeup was done to perfection, giving you a sultry look to your flesh. Your eyeshadow was done smoky and cat-like, accentuating your features. While your lips were painted a deep sanguine color, bringing out the soft plumpness of your natural looks. Your highlighter catching on your cheekbones with every tilt of your face beneath the florescent lights that gave off from the inside, though dimmed out instead for a gentle candlelight deeper in the interior. The contour on your face brought out the natural curve of your face, making you even more beautiful to look at. 

Without your makeup on, everyone would think that you were just another street rat. The soft touch of concealer hid the faint speckles of freckles that danced across your cheekbones and nose, as well as the dark circles that stood out beneath your eye-lids. You had a bit of a reputation for being an insomniac, plagued with memories that only resurfaced once you were asleep. So, you would go long times without sleep.  
You allowed your eyes to drift to a close, breathing in the cool air that the autumn times seemed to bring in from the north. Your arms hugged your body, fingertips warm even though the cold air was bringing your temperature down. 

You relished in the time to yourself, happy that you were at least able to have a few moments to be truly relaxed by yourself. This was quickly brought to an end at the sound of the glass door behind you being gently pushed open, and a knock on the wooden frame bring you from your relaxation.  
"_____, darlin', yer on in 10." A heavily accented voice drew your eyes from their closed position, back to the sight of the shimmering city, and then over towards he who dared to interrupt you.  
Under your blank, intense stare: the male swallowed. His adam's apple bobbing with his obvious discomfort of being under your lidded stare. 

"Mike, you know better than to ruin a girl's fun." You teased him, watching with a playful smile as his cheeks flushed red. Mike O'Connor was a Caucasian Man with a scruffy brown stubble of a beard, leading up to even messier brown hair that was slightly salt and peppered at the sides. He was an older guy, with a lovely wife and an even lovely daughter. He was a good friend of yours, one you cherished despite your reputation and your occupation.  
Gently pushing off of the half-wall, you brushed down your dark red dress. The edges of the silky fabric clinging to your sides and hips as you straightened out the creases that had come from your precarious sitting. Your burgundy heels clicked on the ground as you walked towards Mike, well-manicured hands reaching out to straighten out his collar  
\-- despite the fact that he never wore a damn tie, he always had the first three buttons on his white button-up undone. Leaving him with a messy, rugged look that made people either extremely uncomfortable or wary of his presence.  
He was a pretty good bodyguard, overall. 

Your fingers gently tugged on the collar, righting it to its natural position as your diamond earrings swayed gently. The real gems catching the light beneath the lights as you smirked at the obvious thumping of the male's heart beneath your touch. You were like a deadly animal, to be watched in awe but feared.  
You liked it that way, because it kept many guys grubby hands off of your body. Though, you knew that Dutch would have their fingers removed if they so much as laid a hand on his Siren. You sighed through your nose, plump lips pursing in a frown as you stepped back. 

"...It will be another long night, wont it?" You ask, as Mike hesitantly holds his arm out for you to slide yours through. His other pushing open the glass door and revealing your ears to the soft chatter and laughter that filled the upper parts of the Casino and Lounge. 

"...Afraid so, darlin'." Mike said, regret seeping into his tone as the two of you walk forward into the longue, already many eyes on you as you walk through the candle-lit area. A few regulars tipped their hats or raised their glasses to you, to which you would either give them a wink, a smile, or even blow a kiss in return. It was nice, peaceful. And with Mike by your side, you didn't have to worry about any grubby hands grabbing at your hips or ass to try and cop a feel.  
Leading you up to the mahogany stage towards the center of the lounge, you smile a little brighter at seeing Juan sitting at the grand piano, as well as the rest of his ensemble standing with him. "Boys," You purred out as you approached. Juan gave you a wink as the others said their own greetings.

Juan Carlo, one of your other acquaintances in this hell of a life, a hardworking man and a man of music at his heart. He was a elegant dance partner, and had a beautiful voice to boot too. You would often dance with him, when the lounge was quiet just before the hours of opening. Where you knew that you wouldn't be seen by wandering eyes, or loose tongues.  
His band mates, the flirtatious Lucio Reverre, the bassist; the ever so polite Paolo Rivera, the saxophone player and finally the boisterous Toni Jackson -- the trumpet player. Each boy gave you their own greeting, as Mike held your hand delicately to help you step up onto the stage.  
" _Mi reina_ , your beauty knows no bounds as usual." Juan purrs out to you, tipping his hat as your laughter joins him on stage. Taking your delicate hand off of Mike's, He shoots a warning look towards Juan with an added growl to make the Spanish man lean back with his hands up as the universal sign of 'I mean no harm'. 

Snorting, you roll your eyes as your delicate hands work themselves around the mic stand.  
"Juan, please, you've been trying to sleep with me since day one -- maybe you'll get to keep your fingers if you learn to stop." You say, still teasing as you knew he flirted all out of good fun. Chuckling, the Spanish male winked at you with a finger held over his lips. "I won't tell if you don't, _Princesa._ " 

Giving Mike a subtle nod and shooing motion with your hand, your eyes move from the boys behind you as they go to work setting up their instruments. Your half-lidded eyes scan the sea of people, men in their three piece pin-striped suits sit at the tables haphazardly, drinking and discussing the days events or the business they were doing. There were women strewn about as well, dressed up to the teeth in the finest dresses and jewels -- their make-up was gaudy and heavy. Making them look more like clowns than beautiful, sexy women. It made you want to gag, knowing they were fine going out in public like that. 

You didn't bat an eye at any of them, though you tended to linger on the rare monster here and there. 

There was a dog monster sitting in the back with a couple other dog monsters, playing a round of poker being dealt by one of the many dealers the place hired. A game of pool was being played as well by a water-horse monster in a dark suit, laughing wetly as his human companion scowled at the perfect play of the monster. A bunny monster sashayed by in a tight, skimpy dress as she headed towards the bar where another one of your friends served, Luna Del'Rey, and chatted with a water elemental that was a dark blue-green in color. 

If you hadn't been looking so intently at the people in the lounge, getting a feel for the audience you were about to preform too, you would have never caught the sight of a skeleton monster sitting on his lonesome at one of the many mahogany tables. He was dressed in a black and red pin-striped suit: Suit Jacket the darkest shade of black you have ever seen, with a bright red button-up shirt and a dark tie. Falling down into matching dark pants and dress shoes, strangely: with the laces untied! He also had accompanied a black fedora that had a red ribbon around the base.  
His white bones were tinted orange from the candle-light on the table and he seemed to be nursing a hard whisky as his eye-lights were glaring at the table. Sharp fingers picking at the wood. Staring a moment longer, you caught the glint of the gold tooth in his frowning mouth -- jaw full of rows of sharp teeth. 

Your eyes narrowed at the sight of a concealed weapon beneath his suit coat, barely catching the glint of the metal as he shifted to turn and glare at the entry way into the lounge. Was he waiting for someone, perhaps? Well, better make his time _worthwhile._

Turning back to Juan, you leaned over to whisper your first song into his ear. Your plan getting set in motion as he sent you a sultry grin in return, one that you reciprocated as you turned your eyes back to the people in the lounge.  
Your hands curled around the mic stand, leaning your plump sanguine lips towards the mic itself as the music set into its pace. 

\----

Red did _not fucking like_ getting stood up.  
The growl that grew in his chest was quenched only by the alcohol that he poured into his mouth, the hard whisky helping him stifle the anger that swelled in his chest. His fingers tapped the deep mahogany table beneath him, only a light by the candle light that stretched across the top. The whole room was softly lit with candles and, Red had to admit, that it was a fucking nice place.  
If it weren't for all the looks that he was being given from each end of the room, humans staring at him in either interest, fear, anger or even all three. The dogs in the corner of the room had given him nods of respect when he had walked in and sat down at a table. He was quickly served a drink, the waitress looking at him a little uncertainly but that didn't stop him from giving her a good natured drink. Whisky wasn't his normal drink of choice, but he doubted that this human establishment would give him a bottle of mustard like Grillby's would. 

Snapping back to his thoughts, he grit his teeth together and narrowed his eyes. His red eye blazing with anger, causing a faint red hue to appear around the pin-prick. If he didn't know any better, he would say that he was brought here for a purpose. No, but these human investors wanted to reach out to them on their own turf. Fuck Boss for making him go to this thing alone, saying he could _"handle it"_ if things got bad.  
He scoffed, shaking his head a bit and scratching at his cheek with a scowl. These humans had chosen to meet him here and they were fucking standing him up?! They better damn well know who they were dealing with, he swore to the stars... 

A gentle hush resounded across the lounge, causing Red to look up from his drink in mild confusion. The fuck? why in the hell was everyone getting quiet....now.....?  
His eye-lights naturally moved away from his staring, after glancing around at the others in the lounge bar, his froze as a sweet voice came out of nowhere. 

**"I want a lip**  
And then I want another lip  
I want two lips  
To kiss me all the time.." 

Turning his head, his anger fizzling out slowly as his eyes came onto one of the most beautiful humans he has ever seen. His jaw growing slack at the sight of the beautiful girl, standing with her hands delicately holding onto the mic-stand. Her hips lightly swayed, the red of her dress accenting her skin perfectly along with the make-up that made her even more beautiful. Red felt his hands twitch, something inside him squeezing at the sight of this human. She swayed across the top of the stage, her hands pulling that mic from its stand as she wandered from side to side.  
Leaning over, her fingers lightly traced the face of a man sitting closer to the stage than he was. For some reason, a dark spark of something grew in his chest at the sight. Only to be quickly washed away as your body retreated away from him. 

The dangle of your earrings shining beneath the soft candle light kept him entranced, as he stared at your sanguine-colored lips with a fascination that he didn't know that he was able to have.  
_'Get a fuckin' hold of yourself!'_ he cursed to himself, mentally smacking himself. He was sure he looked like an idiot, slack-jawed and staring at a human like she was the most beautiful thing that he had ever seen. Which, wasn't actually far from the truth but he wasn't gonna fuckin let himself think that way!

 **"I want an arm**  
then I want another arm  
yeah, I want two arms  
To hold me all the time.."

Your arm came and wrapped around yourself, as you swayed with the music. Your body perfectly moving and turning and sashaying with the music playing. Despite his thoughts, Red couldn't help but become totally entranced by you. Leaning his head into his hand as you preformed with a mischievous twinkle to your eyes, something that he thought were like precious gems -- and damn, your lips? Full and red like an juicy apple. He felt his own tongue trace his teeth in the anticipation of what those sweet-looking lips would feel like on his own mouth...  
_'fuck'_

 **"In other words I want a man**  
Yes, a man  
A Man who's all in one,  
We'll put our lips together, close together  
And we'll have so much fun.." 

Your eyes found his in the longue, not all that surprised to see him looking at you like he had seen something shocking. You had often been told your voice was that of an angels, or a soothing stream of water, or even that of a goddess herself. You had been given so many compliments that they all melded into background noise. Your voice was just something that drew others to you, but as soon as they got to know you, they left as quick as they came. 

You let your eyes close half-way, quirking your lips in the skeleton man's direction with a tiny cock of your head. That made his jaw snap back shut finally, and you thought you could see a faint red spread across his cheek-bones. 

Carefully, you stuck out your leg as you stepped off the stage. You could hear Mike stumble out a stammer of confused words, as you rarely ever stepped off the stage without permission from before. You knew you would get some shit for this, but you couldn't help it. Singing as you slowly swayed towards that skeleton monster, your free hand gently brushing past the shoulders of men as you walked with a purpose. Keeping a curious light to your eyes, you slide yourself into a sitting position on the monster's table as you sung. Dress climbing up your leg as you stared into his eyes with a purpose. 

**" I want two lips**  
To kiss me like you're kissing me  
Honey, can't you see?  
Yeah yeah, you're the one for me..."

You reached out a hand, dragging a finger up the side of the skeleton's cheek. Feeling a buzzing of magic beneath your fingers, as you gave him a sultry smile alongside your lidded-gaze. Successfully bringing out more of that red into his skull, sliding off the table. You walked around him, carefully dragging your hand against his skull as you did. Feeling his body shiver beneath your finger-tips as your hand touched his shoulder. Then, just as quick as you came --  
you were gone. 

Strongly swaying your way back to stage as you sung just as strongly as you had been, knowing the eyes on your backside only got worse the more you moved your hips. Were you a tease? yes, yes you were. You had to learn how to squash down that stammering anxious girl deep into the back of your brain when you had to sing and preform.  
You had to be taught just how to wrap them all around your fingers. 

**"In other words I want a man who calls my name**  
Every morning and every night  
I'll hang his picture in my private hall of fame  
And he's gonna treat me right."

you purred as you stepped back on stage, leaning against the beautiful polished piano behind you as you locked eyes with the skeleton again. A flabbergasted, flushed look to his face. Interest could easily be read despite the confusion and lust you could see, and you allowed your normally Stoney expression to express that same interest. Flashing him a quirky smile as you finished your first song of the evening. 

**"I want two lips**  
**To kiss me like you're kissing me**  
**Honey, can't you see?**  
**Yeah yeah, you're the one for me..."**

You hummed idly as the band behind you continued to play their chords, eventually growing softer and softer until the crowd in-front of you broke out into gentle clapping and a few cat-calls here and there. You smiled, flashing a wink to the crowd as your heels gently clicked on the stage. Your eyes meeting those same eye-lights from across the room, surprised to find that they had turned small and white in the moments between your song and dance. Before flashing back to that strong red in his left eye, as if he realized what he was doing. 

Smirking with your full lips, you continued on with your set throughout the evening. 

\----

The night went on just like any other, your set going wonderfully like usual. A nice tip here and there, placed into the hat that laid at the front of the stage. You had glanced at it mid-set to see a nice stash of some 20s and 10s, making your stomach flutter with delight. You would be good tonight.  
Throughout each of your songs, you would migrate close to the skeleton monster you so easily flirted with. But never going as bold as to touch him like you had at the beginning of your song, but your eyes would simply catch his every so often. 

Your mind was drawn away, having finished your sets a little while ago you now had just a few minutes before you knew that Dutch would send for you to do your _other_ job. You sighed, flagging down a waiter and whispering your request in his ear. 

In the time between your set and your next few moments of freedom, Mike had walked back over to you to help you off the stage.  
"what the hell was that?!" he whisper-hissed into your ear, eyes lit in panic. "Mike, relax." you placed your hand on his shoulder, the faint zap of magic under your fingertips descending into his body and forcing his body to relax. 

"traitor.." he muttered, leaning away from you and offering you his arm like before. Shaking your head, you patted his cheek with a soft hand. Not missing the hitch in his throat as he stared at you with honey brown eyes. "I only have a little bit of freedom, Mike. I want to be on my own, tonight." You explained, despite the way his lip curled into a defensive sneer. He didn't like the idea of you being on your own, but he had to listen to you -- unfortunately, in his opinion. 

He grumbled about it, just as that same waiter came over and handed you a glass of whisky and a wine-glass, filled with a deep red wine that made your throat already tingle in anticipation of the rich liquid. Turning back to Mike, you gave him a lazy wink. "I can handle myself fine, _dad._ " you teased, before you made your way back to that same skeleton that was still seated alone. Though now, he was looking off with a spaced-off expression.  
Delicately, you placed down the whisky in front of him. Catching his attention almost immediately as his eye-lights snapped up to you, with your easygoing smile being shown to him in return. 

"Hey there." You purred, "Seems like you had gotten a little low there, bud." Your hand released the whisky glass, glancing back at the sliver of alcohol left in his previous glass. You set your own wine-glass on the table, and already you saw the question brewing in his eyes before you set yourself in the plush seat facing him. Watching his confusion melt away into surprise as you picked your wine-glass up, sipping delicately on the delicious wine. 

There was a few moments of silence, with the both of you getting a good look at eachother before you cracked into another smile.  
"Got stood up, huh bones?" that sure knocked his brain back into place, jolting at your words before narrowing his eyes at you. "Huh?" His voice was gravely, deep and scratchy in a way that it was either overused or underused. Whichever it was, made a surprised jolt of delight down your spine. "You were glaring pretty hard at that door earlier," you nudged towards the entrance with your glass.  
"So, you get stood up or you just like to glare at doors?" you ask, sipping on your drink with a smile as a barely audible growl escaped the monster. "none of ya business." He grunted, leaning back into his chair as he eyed the drink you gave him. 

Scoffing, you cross one leg over the other with a roll of your eyes. "Geez, bones, can't blame a girl for being curious. Guess you just can't _handle_ the questions." You could practically hear Mike groan from across the room. Ah, puns, your classic go-to distraction. Surely that would make the skeleton even angrier--  
He let out a snort, sharp grin curling up the faintest bits as you stared at him surprised when he began to chuckle. "oh, doll, that's just a- _door_ -able." He replied, and you felt your smile growing before you could stop it. Letting a few laughs escape breathily. 

"A kindred spirit!" You said, a real smile touching your lips. It had been a while that you felt genuinely happy, and that spark of happiness that you felt in your heart was quickly stamped out. "I guess I'll have to touch up on my puns, then." 

The skeleton monster's grin grew wider, a lazy shrug given to you in return as he cradled his new drink in his hand. Giving it a small sniff, he deemed it alright and greedily drank the liquid. Your fascination only grew as you watched him take a swig of the hard whisky, and it showed in your eyes and posture as you leaned your head on a hand.  
Blinking his eye-lights at you, he smirked. "see somethin' ya like, doll?" he purred, bringing a faint pink to your cheeks -- but you grinned back at him, idly musing:  
"Oh, I have." 

You winked at him, watching his eyes open wider as his cheeks took on a faint red hue. His mouth snapped shut and he grumbled, unhappy he was beaten at his own game.  
You couldn't help but laugh, seems he had never had his own medicine thrown back at him. When you calmed down again, you fixed your posture to hold out a hand to the well-dressed skeleton. His eyebrow...eye bone? raised at the sight of you holding out your hand.  
You grinned, quirking your own eyebrow. "I'm _____, though, around here you'll hear them call me the Siren." You held his gaze as the skeleton eyed your hand, before slowly raising his own with a grin. "Red," He said, before your hands connected and a jolt of shock rushed up your arm. Gasping, you let go of his hand to look down at your own before hearty laughter built up in the skeleton across from you. 

Clutching his head with his other hand, you looked at him with a small pout as he showed the joy buzzer that rested in his hand. "Ah, the joy buzzer in the hand trick. Classic." He snickered, looking at you with faint red specks in the corner of his eye. Slowly wiping them away with a phalange as you joined him for a second with your soft laughter.  
"I'll admit it," you snicker. "You got me there, Red."  
Something in his eyes lit up as you said his name, shrugging his shoulders again as he set his hand down on the table. The other scratching at his cheek as you smiled at him, sipping delicately on your drink as you kept an eye on him. "yea doll? well, aint that _shocking_." He chuckled, and you smirked back at him. "Yeah, it was a real _kicker_." You replied, giving a half shrug as he jolted with laughter again. Already half-way through your drink, you still regarded the skeleton with interest. 

"Though, I still am curious. Did you get stood up?" You frowned a bit, finger gently swirling the rim of your glass as Red grumbled. "fuckin' assholes haven't shown.." He tossed a glare to the door, fingers tapping an impatient rhythm on the table. "Ah, business or pleasure?" You smiled, tilting your head. "business." He barks out, narrowing his gaze at you before he grinned. "still, got a nice dame like ya to keep me from boredom, ay doll?" He purred, giving you a lazy wink as your cheeks flushed.  
"I wouldn't get your hopes up, bones." You smirked. "My boss doesn't like anyone messing up the merchandise." The way you spoke was a warning, one you often gave those who dared strike up a flirtatious comment with you. Though, Red seemed unperturbed. "I ain't afraid of yer boss." there was an underlying tone to that, but you ignored it instead to change the subject. 

The two of you fell into comfortable conversation, quickly finishing your wine while he still nursed his drink. The topics ranged from the lounge itself to small questions about eachother. So far, you found out that Red had a younger brother and a big extended family. He also seemed to have a addiction to mustard, of all things. He skirted around questions about his work, however. Which only added to the intrigue you felt about him. The two of you laughed at a stupid joke the skeleton made, and you opened your mouth to give him one of your own before a hand gently settled onto your shoulder.  
Bristling, you turned your head slowly only to relax at the sight of Mike. Who was trying his best not to appear apologetic in front of Red.  
"Hey darlin'." he drawled, and you felt Red stiffen and the air grow tense briefly. "Boss wants ya in the back. Ya need to yet ready for your later sets.." He casted a glance towards Red, to which you shrugged off and spoke to him with your eyes. _'don't be sorry, mike.'_

"Well," You drawled, standing up slowly and brushing off your dress a little. Turning to look at Red with an apologetic expression. "I guess this is where our conversation ends, bones."  
Shrugging, Red leans back into his seat. "you gotta do what you gotta do, doll." he gazed at you, something strangely intimate about his hazy eye-lights. Sometime through your conversation they had gone to a neutral white pin-prick, but quickly changed back to the one red eye as he glanced at Mike's hand still on your shoulder. 

"I'll see you around, then?" You ask, smirking as you lean over and press a chaste kiss to his cheekbone. Feeling him freeze up beneath you, your arm sliding into Mike's as he lead you away from the floor and into the dressing rooms. Your debriefing given to you on the way, not looking back at the skeleton who now had a lip-stick stain on his cheekbone. Phalanges touching his cheek with a dumbfounded expression before stretching into a wide grin, fangs glinting in the candle-light. 

"oh, you'll see me soon, doll. _Very soon._ "


	2. the lady in red

**Summary for the Chapter:**

> Well, you certainly weren't expecting the company--
> 
> "well now, what's a pretty dame like you doing in a place like this?"

"What the hell were you thinking, _____?!" Mike whispers violently to you, eyes blazing with a mixture of anger, fear, and caution. The two of you have walked away from Red's table, heading across the lounge and into the back rooms that lined the upper floor of the building. Calmly, you give the frustrated man's arm a small squeeze of reassurance -- at least, it would have been reassuring but it seems to not do much to help. "Mike." You address him calmly, stopping in the middle of the dimly lit hallway and turning to him with a level-headed expression.  
"It is fine. I am fine, see? not a scratch or a mark on me." You state, slipping out of his grasp to do a little turn around in his field of view, letting him see your perfect dress and complexion. He narrows his eyes at you, hands coming to rest tightly against your shoulders. The feeling of fingers squeezing at your skin causes you to tense up, leveling your bodyguard with a dark glare. The edges of your eyes narrowing as you kept your stance tall and your feelings clear through your eyes. If he dared to lay his hands on you and mark your skin, Dutch was going to have him beaten six ways from Sunday! 

Standing in front of him, you cross your arms across your chest and lean a little on your hip. _"Mike."_ You warm him with your voice, watching the way his eyebrow twitches at the sound of his name. "It was a drink and some good company, nothing more -- nothing less. Do you really think I would jeopardize myself like that?" You ask, watching his form start to tense and relax repeatedly. You keep your gaze level with his, not budging from your opinion. The two of you stand in silence for a little while, before he lets out a deep sigh. One you recognized as a sigh of resignation.  
"I'm just tryin' to take care of ya, darlin'." He mumbled, letting your shoulders go to stuff them in his pockets. Eyes narrowed at the ground before him, as he scuffs a boot across the floor. You resist the urge to laugh, but allow a small smile to touch your lips -- until, that is, he keeps speaking. 

"Do ya even know who that is?" He asked, well, more like hissed. His eyes dilated a bit, glancing back towards the entrance of the hallway for a moment before he grabbed your arm, gently this time, and tugged you further down the never ending path as he lowered his voice to a harsh whisper. "That was fuckin' Red Calibri. Y'know, the one who's brother is a _fuckin'_ lawyer?" He hissed out. You blinked softly, letting your mind process the words. Carefully, you move your arm out of his and walk alongside him. Hearing your heels clack against the wooden floor beneath you. "Red did mention that he had a younger brother, but work was something he dodged talking about." You said, hearing your earrings chime gently as you tilted your head. 

_"Of-fuckin'-course."_ You hear Mike hiss beneath his breath, rubbing a hand across his face and scratching at his scruffy beard. "Does Edge Calibri Ring a bell? He's put more of our boys behind bars than any prosecutor in Ebott!" He said, throwing a hand into the air in exasperation. You pause, a waver to your steps as the name suddenly rings a bell.  
Edge Calibri is known for his ruthless tactics as a prosecuting lawyer, as well as a defense lawyer whenever some boys from monster gangs inside the city were suddenly found out. Your lips curl into a frown. Mike was right that the prosecutor has put more and more of your boys behind bars, but in his own defense -- he was damn good at his job. He was intimidating, loud, and smart. You once attended a court proceeding for one of your boys, sitting in the audience with your boss at your side to see the fabled monster yourself. To say you were interested would be a understatement. 

"All the more reason to get closer to him, then." You said calmly, gazing forward at the end of the hallway as the large wooden doors to your boss' office came into view. "Listen, Mike," The two of you paused outside the doors, Mike's hand resting on the door to get ready to open it for you. Leveling a stern stare at him, you lower your voice. "You will not speak of Red to the boss, do you hear me? You know how he is with those who seem interested, and I do not want another _friend_ to learn his wrath again." You watch your bodyguard flinch, hand twitching beside his hip as he glanced away. _"Are we clear?"_  
"...Crystal." The Caucasian man mumbled, before pushing open the door to your personal hell. Putting on your neutral face, you nod at Mike before turning to enter the softly lit office with the grace and poise of a woman. The wooden door shutting behind you and blocking you off from your one source of protection in this place, leaving you to face your other world _alone_. 

\----

The street lights dotting the pathway from The Skyline, the lounge and casino smack dab in the middle of Downtown Ebott, also known as Neutral Territory. However, despite it being known as a place of neutrality, you knew who really ran the streets surrounding the casino. You sigh, watching the air condense in front of your mouth, giving little puffs as you tug your warm fur coat around your body some more.  
You were still dressed in your beautiful dress, your heels gently clacking against the concrete as you walked away from downtown and into the gang territory that surrounded the 'neutral' territory. 

Ebott City was run by many underground groups, or not so elegantly stated -- gangs. There were many smaller gangs, always trying to get their piece of territory -- but then there were the big ones. The ones that had different parts of the city in the palms of their hands. The four major groups each had their own territory, their own piece of the city that they claimed for themselves. The biggest gang of the city used to be Bulldog's gang -- The Hound Dogs -- but recently a monster gang has been taking over territory from them and making a real name for themselves. The Phantoms, a monster run gang has been slowly taking over territory from the mobster and thrusting them off their throne.  
Seeing how the gang was falling apart, another gang has been taking some of their territory as well. Angels Trumpet, run by Madame Daphne. This was the group that ran most of the whore-houses and nightclubs. Their boss is as cunning as she is beautiful, with a sharp tongue to add to a slender face. You had the pleasure of dealing with her once and twice, needing someone to teach you the ropes of seduction that you still hadn't gotten quite down. She was a dear friend now, and a close ally to the group that you affiliated with. Blood Moon, the hidden mob in the neutral territory and a good portion of downtown Ebott. You ran most of the illegal trades business inside and outside of the city, with jobs such as moving packages of even people if the price was right. You also had several divisions within the organization, one of which you became a prodigy at. The Cleanup Division takes care of all the...nasty dealings one might come across. You take out the weeds, and plant the new flowers.

You stifle a laugh, the street lights flickering in and out as you get further away from the safe zone. Your fingers curl around the front of your coat, a tune humming in the back of your throat as you continue onwards through the silent and still streets. You knew, however, that the streets were far from abandoned. The hair on the back of your neck raised gently, alerting you to the gaze of someone as you pass by different alleyways. Faint noises of moving cans and quiet groans of pain echoing back at you. Your SOUL ached in your chest, and you raised a hand to cover where it lay as an attempt to soothe it.

This part of the city was dangerous. There were street kids and gangsters around every corner. This was once formerly Bulldog's territory, now belonging to a smaller gang that had taken the territory for itself when The Hound Dogs started to fall apart.  
They were encroaching on both Blood Moon territory and Lily territory, a mutual displeasure to both groups. 

It was your job to _clean it up_.

The night was cool on your heated flesh, the feeling of being watched only growing stronger the further you walked into the territory. You could hear a few wolf whistles from gangbangers across the street, and you allowed them a sultry smile in return as you continued on your way. Luckily, they did not take that as an invitation to bother you. So you were left to your own devices. Finally, you made your way to the meeting spot. Standing on a street corner, beneath a flickering street light, just like all the movies where the girl gets taken and killed by some wackjob.  
You were not that kind of girl. 

A breeze brushing past your arms made you shiver, tugging the fur coat around you more as you gently leaned against the street light and delicately observed your surroundings. The feeling of being watched tingled at the back of your neck, and you subtly ran a hand through your hair to soothe the nerves that built up and tensed within you. You were not weak, nor helpless. You had nothing to worry about from a guy who just had some wandering eyes.

A couple feet from you there was a bus stop with a bench, and you didn't take notice to it except for when something shifted in the corner of your eyes. You peeked over, trying to keep your wandering gaze from being noticed only to stop and pause. Sitting on the bench was a well tailored man, wearing a gray pinstriped two-piece and a loosened tie. A hat tipped over his face, hiding most of his features from you but from the metacarpals that were folded neatly over his stomach, he was a skeleton. For a moment, you almost wondered if that was Red sitting there. But from the difference in the suit and the easygoing smile you could make out from beneath the rim of the hat -- this skeleton had straight teeth, not sharp, so there was no way that this was the skeleton in question. 

You almost felt guilty, thinking that a skeleton on the street was the same as one you had seen earlier in the day. 

Turning your head a bit sharply, you hug your coat to yourself and sigh into the night air. What were the chances, running into _two_ skeletons in one day? A billion to none, you would say. Thankfully, or unthankfully, it seemed that this skeleton was dead asleep. From your knowledge, the bus that came through this area wouldn't be here for a while longer so you had no reason to wake the sleeping beauty.  
So you shifted on your heels, gazing across the street in wait for your target to get here. You knew that they were to pass through this area, and it wasn't hard to get the Madame to take her whore off this corner in order to do your job. You were doing it for the best of the mob, after all. 

You almost laughed at that. Yeah, 'best'.  
Your stifled giggles must have awoken the sleeping skeleton, because his quiet snoring died out into silence and when you glanced over there was a white eye-light focusing up at you from the skeleton. Well, you certainly weren't expecting the company -- 

"well now, what's a pretty dame like you doin' in a place like this?" A deep, husky voice draws you out of your lamentation and you stare down at the skeleton. A pink tone rises to the edges of your cheeks, but you don't show the flusterment and hide it with a warm smile. "What's a guy like you doing in a place like this?" you counter, digging your nails into your coat and shuffling on your heels. Your ride would be here any moment, now was not the time to be making conversation.  
"touché." the skeleton chuckles, sitting up with the crackle and pop of a couple bones as he adjust his hat back his face. You are taken aback for a moment at the resemblance of this skeleton to Red, and swiftly turn your curious gaze away. "but I asked first." 

There was a smugness clinging to the skeleton's voice, and you couldn't help the laugh that slipped past your lips. "You got me! Ah...I'm just waiting for my ride, sir. It should be here any moment, now." You reply, keeping it as vague as possible. He seems to buy it, eye-lights traveling up and down your form as he pushes off of the bus stop bench and shoves a hand into his pocket. Holding the other out to you, he shuts one eye in a wink. "well, maybe we can wait together. seein' as we're both waitin' for somethin' here." He says. "the names sans. sans the skeleton." He states, and you take a moment to observe the hand outstretched before meeting it with your own.  
"_____." You give him your name in return, not thinking that you would ever run into him again. "You're waiting for your bus, right?" You ask, watching as he nods and shoves his now free hand and into his other pocket. The lazy, relaxed grin on his face putting you into a more cautious state. He stands next to you as you stand on the corner, amusing his presence with your own. 

"Well the buses tend to run longer in this area than most." You say, resuming the tugging on your coat as you look at the streets. A car passes by the both of you, the headlights catching your gaze before filling you with a disappointment and annoyance when it turns out to not be your car. You huff, puffing a fresh breath of air into the cold night. "Thanks to the activity in this area, They tend to dread coming 'round here." You mumble, remembering those old days where you would stand freezing at the bus stop hugging yourself tight -- only to get passed by the bus because there were a couple of gangbangers in the area.  
"oh?" there's a strange amount of curiosity in that tone. "what kind of activity?" He asks, though that tone suggests to knowing more than he was willing to say. 

You pause, glancing at the skeleton who is giving you his undivided attention while standing beside you. "...This area is known for its mob activity, from what I've heard. People can go missing so easily on these streets." You hum. "especially dames like you, hm?" He retorts cheekily, drawing out another laugh from you. "Well, yes, I suppose. But my pop taught me how to take care of myself. There's no need to worry about me." A tiny, shared chuckle between the two of you allows you to relax a bit. This was just a kind stranger, yes. That was all. 

"so, why wait for your ride here rather than some place warm, huh? you look about _chilled to the bone_ there." Sans says, and the pun almost goes flying over your head before it dawns on you and you cover your lips with a hand. "Oh, stars -- you're a skeleton that -- that makes so much sense." You laugh, and feel the energy change as Sans seems to relax. 

"Well, Sans," You start, after you calm down from your small fit of laughter. "I actually work around here, and my...friend is a little off-put by my boss, so to say." You pick your words carefully, tucking a strand behind your ear. Another car starts to come down the street, and you glance in its direction to catch the look of the shiny black car that cruises across the pavement. It begins to slow down as it nears your corner, and you push down the urge to smirk. The car pulls a few feet in front of you, and the window rolls down to reveal a caramel-skinned man in a nice suit give you a wolf-whistle and motion for you with a couple fingers. A proposition.  
Standing straighter, you shoot a smile towards Sans.  
"Well, Sans dear, this seems to be the end to our conversation." You say, dropping your hands to your sides. "...seems so." the skeleton replies, shoulders squaring at the sight of the black car. "Get home safe, okay? It can be dangerous out there for a skeleton." You give him a wink, beginning your walk to the car as the suited skeleton looks at you with an unreadable expression. "...you too, doll." 

The man inside the car smiles at you with a lecherous grin as the door is popped open and you slide inside, hooding your gaze as the window rolls up behind you and the car starts up down the street once more. Leaving behind a skeleton standing on the street corner, and a flickering street lamp. You don't notice in the mirror when within moments, that skeleton disappears into nothing. 

There was no time to be thinking about skeletons any more. You smiled, leaning on the man with a sweet smile. A pretty little thing for him to show off, even if you knew that would not be how this night would end. 

You had a job to finish after all.

**Notes for the Chapter:**

> WOW I didn't mean to take this long to update uhhh  
> sorry?? Q u Q

**Author's Note:**

> this is my first story on here and wow, its gonna be dark.  
> I write a lot of undertale fanfiction so be prepared >:3
> 
> LIST of Nicknames:  
> Classic / Sans - Undertale Sans  
> Orange / Papyrus - Undertale Papyrus
> 
> Red - Underfell Sans  
> Edge / Boss - Underfell Papyrus 
> 
> Stretch - Underswap Papyrus  
> Blue / Blueberry - Underswap Sans
> 
> Black - Swapfell Sans  
> Rus / Mutt - Swapfell Papyrus


End file.
